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Chapter 11: Q32. (page 450)

Question: Enamines and imines are tautomers that contain N atoms. Draw a stepwise mechanism for the acid-catalyzed conversion of enamine X to imine Y.

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01

Step-by-Step SolutionsStep 1: Enamine and Imine

In enamine, there is a lone pair of nitrogen, and it’s bonded with an alkyl group. Imine has a carbon-nitrogen double bond. Imines are more stable than enamines.

02

Enamine hydrolysis

Enamine hydrolysis is the reverse of enamine formation. The lone pair of nitrogen drives the reaction, and a CN bond is formed with nitrogen carrying a positive charge.

The H-N conjugate base bond is cleaved, forming a carbon-nitrogen double bond.

Mechanism of acid-catalyzed conversion of enamine to imine

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Most popular questions from this chapter

Question: When alkyne a is treated with NH2 followed by CH3 , a product having the molecular formula C6H10O is formed, but it is not compound B. What is the structure of the product and why is it formed?

Question: Explain why the C=C of an enol is more nucleophilic than the C=C of an alkene, despite the fact that the electronegative oxygen atom of the enol inductively withdraws electron density from the carbon-carbon double bond.

Question: How is each compound related to A? Choose from tautomers, constitutional isomers but not tautomers, or neither


A.

Question. Give the structure corresponding to each of the following names.

a. trans-2-ethynylcyclopentanol

b. 4-tert-butyldec-5-yne

c. 3,3,5-trimethylcyclononyne

Question: Devise a synthesis of CH3CH2CH2CHO from two-carbon starting materials.
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